Combine the brown sugar, vinegar, Worcestershire sauce and tomato sauce in a small bowl. Heat the EVOO in a large skillet or Dutch oven over medium-high heat. Add the beef and cook until well browned. Season with salt and lots of pepper. Add the garlic, bell peppers and onions and cook, stirring, for 5 minutes. Pour the tomato mixture over the beef, add the beef broth and stir until well combined. Simmer until thickened, 5 to 10 minutes.
Meanwhile, cook the macaroni in a large pot of salted boiling water until not quite tender, about 5 minutes. Drain and add to the sauce. Pour the mixture into a casserole dish and top with the cheese.
Bake until the casserole is bubbling and the top is browned. Top with the pickles and serve from the dish.
The unbaked casserole can be covered and refrigerated for a make-ahead meal. Bring to room temperature and bake as directed before serving.